CA1082717A - Acides benzoiques et procede de preparation - Google Patents

Acides benzoiques et procede de preparation

Info

Publication number: CA1082717A
Authority: CA; Canada
Prior art keywords: benzoic acid; methyl; ethyl; carbon atoms; preparation
Prior art date: 1976-09-04
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA286,018A

Other languages

English (en)

Inventor

Rudi Weyer

Volker Hitzel

Ernold Granzer

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Hoechst AG

Original Assignee

Hoechst AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1976-09-04

Filing date

1977-09-02

Publication date

1980-07-29

1977-09-02 Application filed by Hoechst AG filed Critical Hoechst AG

1980-07-29 Application granted granted Critical

1980-07-29 Publication of CA1082717A publication Critical patent/CA1082717A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 29
235000010233 benzoic acid Nutrition 0.000 title claims abstract description 14
238000002360 preparation method Methods 0.000 title claims description 19
150000001559 benzoic acids Chemical class 0.000 title abstract description 9
150000001875 compounds Chemical class 0.000 claims abstract description 21
150000003839 salts Chemical class 0.000 claims abstract description 19
150000002148 esters Chemical class 0.000 claims abstract description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 29
239000005711 Benzoic acid Substances 0.000 claims description 18
-1 5-(2-aminoethyl)-2-methyl benzoic acid hydrochloride Chemical compound 0.000 claims description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 11
150000002367 halogens Chemical class 0.000 claims description 11
239000000126 substance Substances 0.000 claims description 11
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 9
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 7
150000001412 amines Chemical class 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 5
UEHULQVSTMZZCG-UHFFFAOYSA-N 2-methyl-5-[2-(3-phenylprop-2-enoylamino)ethyl]benzoic acid Chemical compound C1=C(C(O)=O)C(C)=CC=C1CCNC(=O)C=CC1=CC=CC=C1 UEHULQVSTMZZCG-UHFFFAOYSA-N 0.000 claims description 3
RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
230000003647 oxidation Effects 0.000 claims description 3
238000007254 oxidation reaction Methods 0.000 claims description 3
YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
150000002440 hydroxy compounds Chemical class 0.000 claims description 2
229930192474 thiophene Natural products 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
239000002904 solvent Substances 0.000 claims 5
OCWBOHOPJFTEGG-UHFFFAOYSA-N 5-[2-[(4-chlorobenzoyl)amino]ethyl]-2-methylbenzoic acid Chemical compound C1=C(C(O)=O)C(C)=CC=C1CCNC(=O)C1=CC=C(Cl)C=C1 OCWBOHOPJFTEGG-UHFFFAOYSA-N 0.000 claims 2
ZFOVCSTVYYYRSU-ZZXKWVIFSA-N (e)-3-(4-chlorophenyl)prop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=C(Cl)C=C1 ZFOVCSTVYYYRSU-ZZXKWVIFSA-N 0.000 claims 1
WOGITNXCNOTRLK-VOTSOKGWSA-N (e)-3-phenylprop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC=C1 WOGITNXCNOTRLK-VOTSOKGWSA-N 0.000 claims 1
CEOCVKWBUWKBKA-UHFFFAOYSA-N 2,4-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1Cl CEOCVKWBUWKBKA-UHFFFAOYSA-N 0.000 claims 1
RSINFFVFOTUDEC-UHFFFAOYSA-N 2,5-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC(Cl)=CC=C1Cl RSINFFVFOTUDEC-UHFFFAOYSA-N 0.000 claims 1
229930195734 saturated hydrocarbon Natural products 0.000 claims 1
239000000825 pharmaceutical preparation Substances 0.000 abstract description 2
230000000144 pharmacologic effect Effects 0.000 abstract description 2
239000003814 drug Substances 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 141
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 32
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
229960004365 benzoic acid Drugs 0.000 description 14
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
239000000203 mixture Substances 0.000 description 9
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238000001816 cooling Methods 0.000 description 7
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150000003254 radicals Chemical class 0.000 description 6
238000003756 stirring Methods 0.000 description 6
229910021529 ammonia Inorganic materials 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
150000002825 nitriles Chemical class 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
230000002218 hypoglycaemic effect Effects 0.000 description 4
ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 4
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
AAKIZINULUQHGI-UHFFFAOYSA-N 5-(2-aminoethyl)-2-methylbenzoic acid Chemical compound CC1=CC=C(CCN)C=C1C(O)=O AAKIZINULUQHGI-UHFFFAOYSA-N 0.000 description 2
UTLCUFLGDKUSRE-UHFFFAOYSA-N 5-(chloromethyl)-2-methylbenzoic acid Chemical compound CC1=CC=C(CCl)C=C1C(O)=O UTLCUFLGDKUSRE-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
230000031709 bromination Effects 0.000 description 2
238000005893 bromination reaction Methods 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
206010012601 diabetes mellitus Diseases 0.000 description 2
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical group O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
210000002966 serum Anatomy 0.000 description 2
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
WFBFYCMIBAIDJM-UHFFFAOYSA-N 2-chloro-5-[[(4-chlorobenzoyl)amino]methyl]benzoic acid Chemical compound C1=C(Cl)C(C(=O)O)=CC(CNC(=O)C=2C=CC(Cl)=CC=2)=C1 WFBFYCMIBAIDJM-UHFFFAOYSA-N 0.000 description 1
VKBSMRFOWVCIQI-UHFFFAOYSA-N 2-chloro-5-[[(5-chloro-2-methoxybenzoyl)amino]methyl]benzoic acid Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCC1=CC=C(Cl)C(C(O)=O)=C1 VKBSMRFOWVCIQI-UHFFFAOYSA-N 0.000 description 1
LEBWXJZAWTVKFL-UHFFFAOYSA-N 2-chloro-5-methylbenzoic acid Chemical compound CC1=CC=C(Cl)C(C(O)=O)=C1 LEBWXJZAWTVKFL-UHFFFAOYSA-N 0.000 description 1
NUFWPUPLEABIAW-UHFFFAOYSA-N 2-methyl-5-[2-[(2-phenoxyacetyl)amino]ethyl]benzoic acid Chemical compound C1=C(C(O)=O)C(C)=CC=C1CCNC(=O)COC1=CC=CC=C1 NUFWPUPLEABIAW-UHFFFAOYSA-N 0.000 description 1
WHIHIKVIWVIIER-UHFFFAOYSA-N 3-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(Cl)=C1 WHIHIKVIWVIIER-UHFFFAOYSA-N 0.000 description 1
XRHGYUZYPHTUJZ-UHFFFAOYSA-N 4-chlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1 XRHGYUZYPHTUJZ-UHFFFAOYSA-N 0.000 description 1
LDEALVYCNVCCAY-UHFFFAOYSA-N 5-(2-aminoethyl)-2-chlorobenzoic acid Chemical compound NCCC1=CC=C(Cl)C(C(O)=O)=C1 LDEALVYCNVCCAY-UHFFFAOYSA-N 0.000 description 1
YFQKOOJYQYRSTI-UHFFFAOYSA-N 5-(aminomethyl)-2-chlorobenzoic acid Chemical compound NCC1=CC=C(Cl)C(C(O)=O)=C1 YFQKOOJYQYRSTI-UHFFFAOYSA-N 0.000 description 1
OHCXDCDQXZRVQE-UHFFFAOYSA-N 5-(aminomethyl)-2-methylbenzoic acid Chemical compound CC1=CC=C(CN)C=C1C(O)=O OHCXDCDQXZRVQE-UHFFFAOYSA-N 0.000 description 1
ZHFJIITZHYWVAL-UHFFFAOYSA-N 5-(bromomethyl)-2-chlorobenzoic acid Chemical compound OC(=O)C1=CC(CBr)=CC=C1Cl ZHFJIITZHYWVAL-UHFFFAOYSA-N 0.000 description 1
YHFPEGNMSMYOMS-UHFFFAOYSA-N 5-(cyanomethyl)-2-methylbenzoic acid Chemical compound CC1=CC=C(CC#N)C=C1C(O)=O YHFPEGNMSMYOMS-UHFFFAOYSA-N 0.000 description 1
AWVDWCRCIMAPFY-UHFFFAOYSA-N 5-[[(4-chlorobenzoyl)amino]methyl]-2-methylbenzoic acid Chemical compound C1=C(C(O)=O)C(C)=CC=C1CNC(=O)C1=CC=C(Cl)C=C1 AWVDWCRCIMAPFY-UHFFFAOYSA-N 0.000 description 1
KMLQBMKJQLIBQF-UHFFFAOYSA-N 5-[[(5-chloro-2-methoxybenzoyl)amino]methyl]-2-methylbenzoic acid Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCC1=CC=C(C)C(C(O)=O)=C1 KMLQBMKJQLIBQF-UHFFFAOYSA-N 0.000 description 1
JVLUMHRASWENRU-UHFFFAOYSA-N 5-chloro-2-methoxybenzoyl chloride Chemical compound COC1=CC=C(Cl)C=C1C(Cl)=O JVLUMHRASWENRU-UHFFFAOYSA-N 0.000 description 1
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OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
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DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 1
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239000000843 powder Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
230000001003 psychopharmacologic effect Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
229960003147 reserpine Drugs 0.000 description 1
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910001923 silver oxide Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/38—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Diabetes (AREA)
Hematology (AREA)
Obesity (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)

CA286,018A 1976-09-04 1977-09-02 Acides benzoiques et procede de preparation Expired CA1082717A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEP2639935.9		1976-09-04
DE19762639935 DE2639935A1 (de)	1976-09-04	1976-09-04	Benzoesaeuren und verfahren zu ihrer herstellung

Publications (1)

Publication Number	Publication Date
CA1082717A true CA1082717A (fr)	1980-07-29

Family

ID=5987177

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA286,018A Expired CA1082717A (fr)	1976-09-04	1977-09-02	Acides benzoiques et procede de preparation

Country Status (19)

Country	Link
US (1)	US4182775A (fr)
JP (1)	JPS5331641A (fr)
AT (1)	AT353252B (fr)
AU (1)	AU2855777A (fr)
BE (1)	BE858413A (fr)
CA (1)	CA1082717A (fr)
DE (1)	DE2639935A1 (fr)
DK (1)	DK391677A (fr)
ES (1)	ES461971A1 (fr)
FI (1)	FI772597A7 (fr)
FR (1)	FR2363542A1 (fr)
GB (1)	GB1575358A (fr)
IL (1)	IL52877A0 (fr)
NL (1)	NL7709584A (fr)
NO (1)	NO773047L (fr)
NZ (1)	NZ185078A (fr)
PT (1)	PT66992B (fr)
SE (1)	SE7709905L (fr)
ZA (1)	ZA775333B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS57140754A (en) *	1981-02-24	1982-08-31	Kureha Chem Ind Co Ltd	Dihydroxybenzoic acid derivative and physiologically active preparation containing the same
DE3718765A1 (de) *	1986-06-11	1987-12-17	Nippon Shinyaku Co Ltd	Benzoesaeurederivate
WO2024121709A1 (fr)	2022-12-09	2024-06-13	Pfizer Inc.	Inhibiteurs de la protéase de type papaïne (plpro)
WO2024121779A1 (fr)	2022-12-09	2024-06-13	Pfizer Inc.	Inhibiteurs de la protéase de type papaïne (plpro)

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1047851B (it) *	1960-04-29	1980-10-20	Francesco Svimara S P A	Procedimento per la preparazione di anil derivati di difenil gliossali
US3676447A (en) *	1970-06-24	1972-07-11	Stanford Research Inst	3,4,5-trimethoxybenzamides of phenyl-and pyridylakylamines
BE790859A (fr) *	1971-11-02	1973-04-30	Pfizer	Acides carboxamidobenzoiques comme agents hypolipemiques
US3870715A (en) *	1972-03-09	1975-03-11	Nikolaus R Hansl	Substituted amino ethyl meta benzoic acid esters
DE2500157C2 (de) *	1975-01-03	1983-09-15	Hoechst Ag, 6230 Frankfurt	N-Acyl-4-(2-aminoäthyl)-benzoesäuren, deren Salze und Ester, Verfahren zu deren Herstellung und deren Verwendung
DE2541342A1 (de) *	1975-09-17	1977-03-31	Boehringer Mannheim Gmbh	Neue phenoxyalkylcarbonsaeuren und verfahren zur herstellung derselben
DE2629752A1 (de) *	1976-07-02	1978-01-05	Boehringer Mannheim Gmbh	Neue carbonsaeurederivate und verfahren zu ihrer herstellung

1976
- 1976-09-04 DE DE19762639935 patent/DE2639935A1/de active Pending
1977
- 1977-08-29 ES ES461971A patent/ES461971A1/es not_active Expired
- 1977-08-31 NL NL7709584A patent/NL7709584A/xx not_active Application Discontinuation
- 1977-09-01 GB GB36527/77A patent/GB1575358A/en not_active Expired
- 1977-09-01 US US05/829,876 patent/US4182775A/en not_active Expired - Lifetime
- 1977-09-01 FI FI772597A patent/FI772597A7/fi not_active Application Discontinuation
- 1977-09-02 SE SE7709905A patent/SE7709905L/xx unknown
- 1977-09-02 NZ NZ185078A patent/NZ185078A/xx unknown
- 1977-09-02 DK DK391677A patent/DK391677A/da unknown
- 1977-09-02 IL IL52877A patent/IL52877A0/xx unknown
- 1977-09-02 CA CA286,018A patent/CA1082717A/fr not_active Expired
- 1977-09-02 PT PT66992A patent/PT66992B/pt unknown
- 1977-09-02 ZA ZA00775333A patent/ZA775333B/xx unknown
- 1977-09-02 AT AT634677A patent/AT353252B/de not_active IP Right Cessation
- 1977-09-02 NO NO773047A patent/NO773047L/no unknown
- 1977-09-03 JP JP10540377A patent/JPS5331641A/ja active Pending
- 1977-09-05 AU AU28557/77A patent/AU2855777A/en active Pending
- 1977-09-05 BE BE180683A patent/BE858413A/fr unknown
- 1977-09-05 FR FR7726882A patent/FR2363542A1/fr active Pending

Also Published As

Publication number	Publication date
PT66992B (de)	1979-05-14
ZA775333B (en)	1978-07-26
BE858413A (fr)	1978-03-06
DK391677A (da)	1978-03-05
FR2363542A1 (fr)	1978-03-31
ES461971A1 (es)	1978-12-01
AU2855777A (en)	1979-03-15
DE2639935A1 (de)	1978-03-09
SE7709905L (sv)	1978-03-05
FI772597A7 (fi)	1978-03-05
NO773047L (no)	1978-03-07
JPS5331641A (en)	1978-03-25
NZ185078A (en)	1979-03-28
US4182775A (en)	1980-01-08
AT353252B (de)	1979-11-12
ATA634677A (de)	1979-04-15
GB1575358A (en)	1980-09-17
PT66992A (de)	1977-10-01
NL7709584A (nl)	1978-03-07
IL52877A0 (en)	1977-11-30

Legal Events

Date	Code	Title	Description
1997-07-29	MKEX	Expiry

Publication	Publication Date	Title
US4221815A (en)	1980-09-09	Benzoic acids, their derivatives and process for preparing them
US4181658A (en)	1980-01-01	Certain nicotinamido-n-benzoic acid derivatives
US4238506A (en)	1980-12-09	Hypoglycaemically and hypolipidaemically active derivatives of phenyl-alkane-carboxylic acids
US4207341A (en)	1980-06-10	Hypoglycaemically and hypolipidaemically active derivatives of phenylacetic acid
JPS61267580A (ja)	1986-11-27	チアゾリジン誘導体
IE41724B1 (en)	1980-03-12	Diphenylsulphoxide derivatives
US4006180A (en)	1977-02-01	[1,3-Dihydroxy-2-substituted and 2,2-disubstituted-indanyloxy(or thio)]alkanoic acids
US4542127A (en)	1985-09-17	Antidiabetic salicylic acid derivatives
CA1082717A (fr)	1980-07-29	Acides benzoiques et procede de preparation
US4151302A (en)	1979-04-24	Araliphatic dihalogen compounds composition and method of use
US4845110A (en)	1989-07-04	Organic compounds and their pharmaceutical use
DE2031227A1 (de)	1971-01-07	Neue substituierte Sahcylsauren und Verfahren zu ihrer Herstellung
KR860001887B1 (ko)	1986-10-24	글루타민 유도체의 제조방법
US3927092A (en)	1975-12-16	Amides of 2-{8 halophenoxy (or halophenylthio){9 -alkanoic acids
DE3306146A1 (de)	1983-09-01	Pyridin-derivate und ihre verwendung als arzneimittel
KR100224330B1 (ko)	1999-10-15	골관절 질환의 치료에 유용한 n-((4,5-디히드록시-및 4,5,8-트리히드록시-9,10-디히드로-9,10-디옥소-2-안트라센-일)카르보닐)아미노산
CA1109077A (fr)	1981-09-15	Derives de l'acide 2-hydrazonopropionique et leur preparation
US4057647A (en)	1977-11-08	Araliphatic dihalogen compounds and process for their preparation
US3979402A (en)	1976-09-07	Thiazole derivatives
NZ224294A (en)	1990-12-21	(3,5-di-t-butylphenoxy)-alkyl carboxylic acid derivatives and pharmaceutical compositions
US4230719A (en)	1980-10-28	Novel 2-[4-(3-methyl-2-thienyl)phenyl]propionic acid and pharmaceutically acceptable salt thereof and method for treating symptoms of inflammation and pain
US4126625A (en)	1978-11-21	Certain 5-substituted-3-methyl-2-benzofuran acetic acids
WO1992011234A1 (fr)	1992-07-09	Nouvelles amines, leur procede de production et medicaments contenant ces composes
CA1069900A (fr)	1980-01-15	DERIVES DE LA 1-(3-PHENYLPROPYL)-4-).beta.-ALKOXYACRYLOYL) PIPERAZINE
US4377586A (en)	1983-03-22	Diuretic 2,6-diaryl-4-pyridine carboxylic acids